Tag: M.W:200-300

Synthetic Route of 1353100-91-0,Some common heterocyclic compound, 1353100-91-0, name is Ethyl 3-bromo-1H-pyrazole-4-carboxylate, molecular formula is C6H7BrN2O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of NaH (275 mg, 6.86 mmol, 60% purity) in THF (5 mL) was added dropwise a solution of ethyl 3-bromo-lH-pyrazole-4-carboxylate (1.0 g, 4.57 mmol) in THF (10 mL) at 0 C. After addition, the mixture was stirred at this temperature for lh, and then Mel (2.93 g, 20.64 mmol, 1.29 mL) was added dropwise at 0 C. The resulting mixture was stirred at 25 C for 19h. The reaction mixture was quenched by addition sat. H4CI (5 mL), and then diluted with H20 (10 mL) and extracted with EtOAc (20 mL x 2). The combined organic layers were washed with brine (15 mL x 2), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (Si02, Petroleum ether/Ethyl acetate = 8/1 to 5: 1) to give the Compound 142A (120 mg, yield: 11.27%) was obtained as a yellow oil and Compound 142B (370.00 mg, yield: 34.74%) was obtained as a white solid. (1387) [0574] 1H NMR (400MHz, CDC13) (142A) delta 7.93 (s, 1H), 4.42 – 4.21 (m, 2H), 3.97 – 3.82 (m, 3H), 1.36 (t, J = 7.2 Hz, 3H) (1388) [0575] 1H NMR (400MHz, CDC13) (142B) delta 7.83 (s, 1H), 4.30 (q, J = 7.0 Hz, 2H), 3.94 – 3.86 (m, 3H), 1.41 – 1.28 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-bromo-1H-pyrazole-4-carboxylate, its application will become more common.

Reference:
Patent; BLADE THERAPEUTICS, INC.; BUCKMAN, Brad, Owen; YUAN, Shendong; MA, Jingyuan; EMAYAN, Kumaraswamy; ADLER, Marc; (327 pag.)WO2018/9417; (2018); A1;,
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Application of 39806-90-1,Some common heterocyclic compound, 39806-90-1, name is 4-Iodo-1-methyl-1H-pyrazole, molecular formula is C4H5IN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of l-methyl-4-iodo- lH-pyrazole (3 g, 14.42 mmol) in THF (40 mL) was added isopropylmagnesium chloride (2.0M in THF, 8.00 mL, 16.01 mmol) at O 0C. The mixture was stirred at O 0C for 1 h, cooled to -78 0C and JV-methoxy-Lambda’-methyl-2- ethoxyacetamide (product of Step A, 3.18 g, 21.63 mmol) was added. The mixture was slowly warmed to rt over 1.5 h. The reaction was cooled to -78 0C and quenched by the dropwise addition of saturated aqueous NH4CI. The reaction was warmed to rt and stored in the cold overnight. The reaction was then diluted with cold IN HCl, extracted four times with EtOAc, and the combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography eluting with a gradient of 50% EtOAc/hexanes to 100% EtOAc afforded 2-ethoxy-l-(l-methyl-pyrazol-4-yl)-ethanone. 1H NMR (500 MHz, CDCl3): 6 8.07(s, IH), 8.03 (s, IH), 4.38 (s, 2H), 3.96 (s, 3H), 3.62 (q, 2H), 1.29 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Iodo-1-methyl-1H-pyrazole, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; GUO, Liangqin; LIU, Jian; NARGUND, Ravi, P.; PASTERNAK, Alexander; YANG, Lihu; YE, Zhixiong; WO2010/51177; (2010); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 179692-08-1 as follows. name: Ethyl 4-iodo-1H-pyrazole-5-carboxylate

General procedure: Aryl Halide, tetrakis (triphenylphosphine)palladium or Palladium (II)bis(triphenylphosphine) dichloride (0.05eq) and boronic acid or pinnacol ester (1.2eq) were weighed out into a microwave vessel or sealed tube. Acetonitrile (3mL/mmol) and a 1M aqueous solution of Sodium Carbonate (3eq) were added. The vessel was capped and heated thermally 3-18hrs at 100C. Upon completion, the reaction was cooled and crude product was either triterated via addition of water and collection by filtration or extracted with sat ammonium chloride and DCM. If the crude product was an intermediate, it was taken into the next step in most cases w/o further purification or alternatively submitted for reverse phase HPLC purification when it was a final product.Similar to the procedure as described in General Procedure M, ethyl 4-iodo-lH- pyrazole-3-carboxylate was reacted with 1 -ethyl- lH-pyrazol-4-ylboronic acid to give the title compound (343 mg, 27%) as a yellow oil. LC-MS (ES, m/z): 235 [M+H]+.

According to the analysis of related databases, 179692-08-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; BLAQUIERE, Nicole; CASTANEDO, Georgette; FENG, Jianwen A.; CRAWFORD, James John; LEE, Wendy; LIN, Xingyu; HU, Baihua; WU, Guosheng; (218 pag.)WO2016/135163; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Related Products of 88095-61-8,Some common heterocyclic compound, 88095-61-8, name is 1-Benzyl-4-nitro-1H-pyrazole, molecular formula is C10H9N3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a 8 mL glass vial equipped with a magnetic stirbar were sequentially added K2CO3 (207 mg, 1.5 mmol), the nitroazole substrate (0.50 mmol), aryl halide (0.50 mmol oras indicated), toluene (0.50 M or 1.0 M), Pd(OAc)2 (5.60mg, 0.025 mmol) and [PCy3H]BF4 (18.4 mg, 0.050 mmol).The reaction mixture was purged with nitrogen through aTeflon-lined cap. Then the cap was replaced with a newTeflon-lined solid cap. The reaction vial was moved to a preheatedreaction block. After stirring for 18 h at the indicatedtemperature, the reaction mixture was cooled to 25 C and concentrated. The residue was purified by flash column chromatography to provide the desired arylated product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Benzyl-4-nitro-1H-pyrazole, its application will become more common.

Reference:
Article; Jung, Haeun; Bae, Seri; Jang, Ha-Lim; Joo, Jung Min; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 3009 – 3014;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1226781-82-3, name is tert-Butyl 2-(methylsulfonyl)-4,6-dihydropyrrolo[3,4-c]pyrazole-5(2H)-carboxylate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C11H17N3O4S

3a(2.1g, 7.3mmol) dissolved in dichloromethane (25 ml) in, at 0 C added to trifluoroacetic acid (5 ml), the reaction of the 0 C under 2 hours. The reaction the fluid turns on lathe stem, plus ammonia water (2 ml) quenching the reaction, silica gel column chromatography for purification (dichloromethane/methanol (v/v)=50:1), to obtain white solid3b(1.1g, 80.5% yield).

According to the analysis of related databases, 1226781-82-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LI, CAI-HU; WEI, YONG-GANG; (99 pag.)TW2017/8222; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H7F3N2O2

To a solution of 4-{4-[5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl]thiazol-2-yl}piperazine-2-carboxylic acid methyl ester hydrochloride (0.5 g, 1.0 mmol) in 4 ml of N,Ndimethylformamide were added at 0C sequentially ethyl(diisopropyl)amine (0.3 g, 2.5 mmol), (5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetic acid (0.2 g, 1.1 mmol) and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (0.5 g, 1 .1 mmol). The reaction mixture was stirred for 16 h at room temperature, then poured on waterand extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate and evaporated. The residue is purified by column chromatography on silica gel (cyclohexane / ethyl acetate 4:1) to give 4-{4-[5-(2,6-difluoro-phenyl)-4,5-dihydro-isoxazol-3-yl]thiazol-2-yl}-1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetyl]piperazine-2-carboxylic acid methyl ester (compound I.az.038)as light yellow foam. 1H-NMR (400 MHz, CDCl3): delta = 2.31 (s, 3H), 3.12(t, 1H), 3.34 (dd, 1H), 3.53 (dd, 1H), 3.64 – 3.76 (m, 4H), 3.89 (dd, 1H), 4.20 (dt, 1H), 4.44 (dd, 1H), 4.97 (dd, 1H), 5.22 (dd, 1H), 6.02 (t, 1H), 6.33 (d, 1H), 6.91 (t, 2H), 7.02 (s, 1H), 7.29 (q, 1H). MS:m/z = 599 (M+1).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 345637-71-0.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; LAMBERTH, Clemens; SULZER-MOSSE, Sarah; CEDERBAUM, Fredrik; UMARYE, Jayant; SONAWANE, Ravindra; WO2013/127784; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 285984-25-0, name is 3-(tert-Butyl)-1-(p-tolyl)-1H-pyrazol-5-amine belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below. category: pyrazoles-derivatives

To a stirred solution of CDI (223 mg, 1.38 mmol) in dry DCM (3.5 mL) was added Intermediate A1 (315 mg, 1.38 mmol) as a solid, portion-wise, over 12 min and the resulting solution maintained at RT for 4 hr. An aliquot of this solution (2.0 mL, 0.79 mmol) was added to a solution of Intermediate G1, (140 mg, 0.39 mmol) in dry THF (5.0 mL), and the reaction mixture was kept at RT for 17 hr and was then partitioned between saturated aq. NaHCO3 (30 mL) and DCM (30 mL). The aq. layer was extracted with DCM (30 mL) and the combined organic extracts were dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 12 g, [5% MeOH in EtOAc] in isohexane, 0-45%, gradient elution) to afford the title compound, Example 14, as an off white solid (127 mg, 52%); Rt 5.40 min (Method 1 basic); m/z 611/613 (M+H)+ (ES+); 1H NMR (400 MHz, DMSO-d6) delta: 1.26 (9H, s), 2.37 (3H, s), 3.37 (3H, s), 4.07 (2H, s), 5.31 (2H, s), 6.34 (1H, s), 7.18-7.23 (2H, overlapping m), 7.31-7.34 (2H, overlapping m), 7.38-7.40 (2H, overlapping m), 7.85 (1H, d), 8.21 (1H, br s), 8.33 (1H, dd), 8.60 (1H, br s), 8.95 (1H, br s), 10.01 (1H, br s).

The synthetic route of 285984-25-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; King-Underwood, John; Hardy, George; Murray, Peter John; Williams, Jonathan Gareth; Onions, Stuart Thomas; US2013/29990; (2013); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 345637-71-0, A common heterocyclic compound, 345637-71-0, name is 2-(5-Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid, molecular formula is C7H7F3N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

a) Preparation of 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester To a solution of (5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid (9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45 mL, 216 mmol), followed by O-(benzotriazol-1-yl)-N,N,N’,N’-tetramethyluronium tetrafluoroborate (15.5 g, 39.7 mmol). After stirring 15 min at RT, 2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride (10 g, 36.1 mmol) is added to the reaction mixture. After stirring overnight at RT, solvent is evaporated and the resulting yellow oil is dissolved in ethylacetate (300 mL), washed with saturated aqueous sodium bicarbonate solution (300 mL), 1M HCl solution (300 mL), and brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and evaporated under reduced pressure. The crude mixture is purified by column chromatography on silica gel (dichloromethane/methanol 10:1) to give 2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetyl]piperidin-4-yl}-thiazole-4-carboxylic acid ethyl ester. 1H-NMR (400 MHz, CDCl3): delta=1.40 (t, 3H), 1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1H), 3.22-3.43 (m, 1H), 4.03-4.12 (m, 1H), 4.42 (q, 3H), 4.54-4.69 (m, 1H), 4.93-5.08 (2d, 2H (diastereotopic)), 6.35 (s, 1H), 8.10 (br, 1H). MS: m/z=209 (M+1).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; Umarye, Jayant; Berthon, Guillaume; Cederbaum, Fredrik Emil Malcolm; Luksch, Torsten; Lamberth, Clemens; Sulzer-Mosse, Sarah; Kanjilal, Pranab; Sonawane, Ravindra; US2014/243371; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 1082745-50-3, name is 5-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H14N4O2

To the mixture of 5-amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-carboxamide (Intermediate P6, 0,301 g, 1,55 mmol) and ethyl (2-chlorophenoxy)-acetate (Intermediate P16, 1.663 g, 7.75 mmol) in dry tetrahydrofuran (16 mL) 5 eq. of IM soLution of potassium tert-butanolate in tetrahydrofuran were addedand the whole was heated at reflux for 18 hours. The crude product was isoLated by extraction with ethyl acetate, organic layer was washed with brine and dried with sodium sulphate. The compound was purified by chromatography on silica gel (hexane/acetone, gradient from 100:0 to 0:100). 95 mg of the titLe product were obtained as an amorphous soLid (yield 29.2%).1H NMR (300MHz, DMSO-d6): delta 12.37(5, 1H), 8.09 (s, 1H), 7.47 (m, 1H), 7.31 (m,1H), 7.25 (m, 1H), 7.01 (m, 1H), 5.14 (s, 2H), 4.87 (m, 1H), 3.94 (m, 2H), 3.47 (m, 2H), 2.09 (m, 2H), 1.77 (m, 2H).MS-ESI: (m/z) calculated for C17H18C1N4O3 [M+H]+: 361 .79, found 361 .8.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; CELON PHARMA S.A.; MOSZCZY?SKI-P?TKOWSKI, Rafa?; BOJARSKI, ?ukasz; STEFANIAK, Filip; WIECZOREK, Maciej; DUBIEL, Krzysztof; LAMPARSKA-PRZYBYSZ, Monika; WO2014/16789; (2014); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Electric Literature of 50877-42-4,Some common heterocyclic compound, 50877-42-4, name is 1-Benzyl-4-iodo-1H-pyrazole, molecular formula is C10H9IN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of 4-[7-(1-ethylpropyl)-5-(4-fluorophenyl)furo[3,2-b]pyridine-2-carbonyl]- 3,3-dimethyl-piperazin-2-one (70 mg, 0.160 mmol) in DMF (1.750 mL) were added 1- benzyl-4-iodo-pyrazole (68.18 mg, 0.240 mmol), CuI (15.23 mg, 0.080 mmol) and K3PO4 (67.93 mg, 0.320 mmol). The mixture was degassed for 10 min, then to it was added N,N’-dimethylethane-1,2-diamine (14 mg, 16.91 muL, 0.159 mmol). The mixture was allowed to stir overnight at 100C. The suspension was cooled down, water was added along with EtOAc. The phases were separated to afford a crude mixture of 1-(1- benzylpyrazol-4-yl)-4-[7-(1-ethylpropyl)-5-(4-fluorophenyl)furo[3,2-b]pyridine-2- carbonyl]-3,3-dimethyl-piperazin-2-one (95.0 mg, 100.0%)

The synthetic route of 50877-42-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; SAYEGH, Camil Elie; STURINO, Claudio; FOURNIER, Pierre-Andre; LACOSTE, Jean-Eric; DIETRICH, Evelyne; MARTEL, Julien; VALLEE, Frederic; (494 pag.)WO2016/154075; (2016); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics